1-Tetralone → 4-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

HRID 2356022Notes

Reaction equation

HRID 2356022 reaction equation
[NH2:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][NH:12][C:13](OC(C)(C)C)=O)=[C:7]([N+:20]([O-:22])=[O:21])[CH:6]=1)(=[O:4])=[O:3].[C:23]1(=O)[C:32]2[C:27](=[CH:28][CH:29]=[CH:30]C=2)[CH2:26][CH2:25][CH2:24]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C(O)(C(F)(F)F)=O.ClCCl>[C:13]1(=[N:12]/[NH:11][C:8]2[CH:9]=[CH:10][C:5]([S:2]([NH2:1])(=[O:3])=[O:4])=[CH:6][C:7]=2[N+:20]([O-:22])=[O:21])/[CH2:30][CH2:29][CH2:28][C:27]2[C:32]/1=[CH:23][CH:24]=[CH:25][CH:26]=2

Participants

5

Reactant 3

HCID 107241-TetraloneHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 22730367Tert-butyl 2-(4-(aminosulfonyl)-2-nitrophenyl)hydrazinecarboxylate

Product 1

HCID 96121654-[(2E)-2-(3,4-dihydro-2H-naphthalen-1-ylidene)hydrazinyl]-3-nitrobenzenesulfonamide

Reagents, catalysts & solvents 1

HCID 21863450Trifluoroacetic acid methylene chlorideSolvent

Procedure

A room temperature solution of Example 73A (145 mg, 0.44 mmol) in 1:1 TFA/dichloromethane (10 mL) was stirred for 4 hours and concentrated. The concentrate was dissolved in ethanol (2 mL), treated with 3,4-dihydro-1(2H)-naphthalenone (8.2 mg, 0.06 mmol) and pyridinium p-toluenesulfonate (2 mg, 0.008 mmol), heated to reflux, stirred for 2 hours, cooled to room temperature, and concentrated. The concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane to provide the desired product. MS (ESI(−)) m/e 359 (M−H)−.

Workup

  1. concentrationconcentrated
  2. dissolutionThe concentrate was dissolved in ethanol (2 mL)
  3. temperatureheated
  4. temperatureto reflux
  5. concentrationconcentrated
  6. customThe concentrate was purified by flash column chromatography on silica gel with 4% methanol/dichloromethane

Sources & evidence

ORD record
ord-c966e3af7f11413191a095a41d265862
Source dataset
uspto-grants-2010_07
Patent number
US07754886B2

Reaction notes

Loading…